EP0415203B1 - Colorants thiazoliques du type merocyanine ainsi qu'un procédé de transfert thermique de ces colorants - Google Patents

Colorants thiazoliques du type merocyanine ainsi qu'un procédé de transfert thermique de ces colorants Download PDF

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EP0415203B1
EP0415203B1 EP90115763A EP90115763A EP0415203B1 EP 0415203 B1 EP0415203 B1 EP 0415203B1 EP 90115763 A EP90115763 A EP 90115763A EP 90115763 A EP90115763 A EP 90115763A EP 0415203 B1 EP0415203 B1 EP 0415203B1
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alkyl
formula
radical
phenyl
hydrogen
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EP0415203A2 (fr
EP0415203A3 (en
Inventor
Volker Dr. Bach
Karl-Heinz Dr. Etzbach
Gunther Dr. Lamm
Ruediger Dr. Sens
Klaus Unterforsthuber
Rosemarie Dr. Rausch-Meier
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BASF SE
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BASF SE
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)

Definitions

  • Dyes are known from DE-A-3 524 519 which are produced by oxidative coupling of p-phenylenediamines onto phenols and which are used in thermal transfer printing on coated papers.
  • EP-A-275 381 describes a process for the thermal transfer of cyanovinylthiazoles.
  • the object of the present invention was to provide new merocyanine-like dyes which have a heterocyclic radical.
  • the new dyes should have advantageous application properties.
  • Suitable radicals R1, R2, R3, L1, L2 and L4 are e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • Residues R1, R2, R3 and L4 are further e.g. Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl or isooctyl.
  • R1, R2 and L4 are also e.g. Nonyl, isononyl, decyl, isodecyl, undecyl or dodecyl.
  • Residues R1 and R2 are furthermore, for example, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl (the designations isooctyl, isononyl, isodecyl and isotridecyl are trivial designations and come from the alcohols obtained after oxosynthesis (see , 4th edition, volume 7, pages 215 to 217 and volume 11, pages 435 and 436).) 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3rd -Ethoxypropyl, 2- or 3-propoxypropyl, 2-or 3-butoxypropyl, 4-methoxybutyl, 4-ethoxybutyl, 4-butoxybutyl, 8-butoxy
  • R1, R2, R3 and L1 are further e.g. Phenyl, 2-, 3- or 4-methylphenyl, 2- or 4-isopropylphenyl, 2-butylphenyl, 2-, 3- or 4-methoxyphenyl, 2-propoxyphenyl, 4-butoxyphenyl or 2- (but-2-oxy) phenyl.
  • R1 and R2 together with the nitrogen atom connecting them represent a 5- or 6-membered saturated heterocyclic radical, this can be substituted by C1-C6-alkyl and contain, for example, nitrogen or oxygen as further heteroatoms.
  • heterocyclic residues are e.g. Pyrrolidino, piperidino, morpholino, piperazino, 2-methylpyrrolidino, 3-butylpyrrolidino, 4-ethylpiperidino, 2,6-dimethylpiperidino, 2- (pent-2-yl) piperidino, 2-methylmorpholino, 3-ethyl-5-methylmorpholino, N -Methylpiperazino, N-ethylpiperazino, 3-butylhexahydropyrimidin-1-yl or 3,6-dimethylhexahydropyrimidin-1-yl.
  • Residues L4 are still e.g. Thiazol-2-yl, thiazol-5-yl, 4-propanoylphenyl, 4-pentanoylphenyl, 4- (4-methylpentanoyl) phenyl, 4-ethoxycarbonylphenyl, 4-propoxycarbonylphenyl, 4-butoxycarbonylphenyl, 4-pentyloxycarbonylphenyl or 4- (N- Ethyl or N-hexylcarbamoyl) phenyl.
  • the thiazole dyes of the formula I according to the invention are prepared by methods known per se.
  • Another object of the present invention was to provide a new process for the thermal transfer of dyes.
  • a transfer sheet which contains a thermally transferable dye in one or more binders, optionally together with suitable auxiliaries, on a support is heated with a heating head with short heating pulses (duration: fractions of a second) from the back, whereby the dye migrated from the transfer sheet and diffused into the surface coating of a recording medium.
  • the main advantage of this method is that it is easy to control the amount of dye to be transferred (and thus the color gradation) by adjusting the energy to be delivered to the heating head.
  • a thermal head or a laser can be considered as an energy source in the method according to the invention.
  • a thermal head is preferred.
  • the dyes are processed in a suitable organic solvent, for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or mixtures thereof, with one or more binders, optionally with the addition of auxiliaries, to give a printing ink .
  • a suitable organic solvent for example chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or mixtures thereof.
  • binders optionally with the addition of auxiliaries
  • binders All resins or polymer materials which are soluble in organic solvents and are capable of binding the dye to the inert support in an abrasion-resistant manner are suitable as binders. Preference is given to those binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film without any visible crystallization of the dye occurring.
  • binders examples include cellulose derivatives, e.g. Methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyl resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
  • Polymers and copolymers of acrylates or their derivatives, such as polyacrylic acid, polymethyl methacrylate or styrene-acrylate copolymers, polyester resin, polyamide resin, polyurethane resin or natural CH resin, such as gum arabic are also suitable as binders.
  • Other suitable binders are e.g. in DE-A-3 524 519.
  • Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyrate or polyvinyl acetate.
  • the weight ratio of binder: dye is generally 1: 1 to 5: 1.
  • Inert carriers are e.g. Silk, blotting or glassine paper or plastic films with good heat resistance, e.g. optionally metal-coated polyester, polyamide or polyimide.
  • the inert carrier is optionally additionally coated with a slip layer on the side facing the energy source in order to prevent the energy source from sticking to the carrier material.
  • Suitable lubricants are e.g. in EP-A-216 483 or EP-A-227 095.
  • the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
  • thermostable plastic layers with an affinity for the dyes to be transferred the glass transition temperature (Tg) of which is preferably used as the dye receiver layer
  • Temperature range should be 50 ° C ⁇ Tg ⁇ 100 ° C, eg modified polycarbonates or polyester.
  • Suitable formulations for the receiver layer composition are described, for example, in EP-A-227 094, EP-A-133 012, EP-A-133 011, EP-A-111 004, JP-A-199 997/1986, JP-A- 283 595/1986, JP-A-237 694/1986 or JP-A-127 392/1986.
  • the transfer is preferably carried out by means of a thermal head which must be able to be heated to a temperature of ⁇ 300 ° C. so that the dye transfer can take place in the time range t: 0 ⁇ t ⁇ 15 msec.
  • the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
  • the new dyes transferred in the process according to the invention are generally distinguished by improved migration properties in the recording medium at room temperature, easier thermal transferability, easier technical accessibility, better resistance to moisture and chemical substances, higher color strength, better solubility , higher light fastness and in particular by higher color purity.
  • the resulting blue precipitate was filtered off, washed with water and dried at 30 ° C in a vacuum drying cabinet.
  • Tables 1 and 2 list the thermal transfer parameters T * and ⁇ E T , the absorption maxima of the dyes ⁇ max (measured in methylene chloride), and the binders used.
  • the dyes in Tables 1, 11 and 12 were synthesized according to variant A.
  • Tables 2 to 10 were synthesized according to variant B.
  • the color purity of the dye of the formula was with the color purity of the dyes of the formula known from EP-A 227 096 compared in methylene chloride.
  • the brilliance (chroma), half-width of the main absorption band (HBW) and the color tone (HGD) were determined according to CIELAB in the brightness range L: 60 ⁇ L ⁇ 95. (A comparison of different dyes is only meaningful if the brightness and shade are similar.)
  • the coloristic superiority of the dye 128a results from the values mentioned above.
  • the new dye 128a Compared to the known dyes 128b and 128c, the new dye 128a has a steeper increase in the absorption band and a higher transparency in the blue and green spectral range.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (3)

  1. Colorants thiazoliques de formule I
    Figure imgb0047
     dans laquelle
    R¹ et R²   sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un reste alkyle, qui est éventuellement interrompu par 1 à 3 atomes d'oxygène, alcanoyloxyalkyle ou alcoxycarbonyloxyalkyle, ces restes renfermant chacun jusqu'à 18 atomes de carbone et pouvant être substitués par des groupements phényle, (alkyl en C₁-C₄)phényle, (alcoxy en C₁-C₄)phényle, hydroxy, cyclohexyle ou cyano, un atome d'hydrogène, un reste phényle éventuellement substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄, un reste cyclohexyle ou un reste de formule



            (CH₂-)kCOO-(Y-O-)m(W-O-)vL¹



    où
    k   est mis pour 2, 3 ou 4
    m et v   sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, pour 0, 1 ou 2,
    Y et W   sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, pour un reste alkylène en C₂-C₆ et
    L¹   est mis pour un reste alkyle en C₁-C₄ ou phényle éventuellement substitué par un reste alkyle en C₁-C₄ ou alcoxy en C₁-C₄,
    ou R¹ et R² forment ensemble, avec l'atome d'azote qui les relie, un reste hétérocyclique saturé à 5 ou 6 termes qui peut contenir d'autres hétéroatomes et être substitué par un reste alkyle en C₁-C₆,
    R³   représente un atome d'hydrogène, d'halogène ou un reste alkyle en C₁-C₈, phényle éventuellement substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄, benzyle éventuellement substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄, cyclohexyle, hydroxy, furyle ou thiényle, et
    A   représente un reste de formule
    Figure imgb0048
     où
    L²   est mis pour un atome d'hydrogène, de fluor, de chlore, de brome, pour un reste hydroxy, nitro, alkyle en C₁-C₄, cyano, (alkyl en C₁-C₄)sulfonylamino ou pour un reste de formule COOR¹, CONHR¹, NHCOR¹ ou NHSO₂R¹, R¹ ayant chaque fois la signification indiquée précédemment, et
    L³   est mis pour un atome d'hydrogène, de fluor, de chlore, pour un reste cyano ou pour un reste de formule CONHL⁴, NHCOL⁴, NHCONHL⁴, SO₂NHL⁴, NHSO₂L⁴ ou COOR¹, R¹ ayant la signification indiquée précédemment et L⁴ représentant chaque fois un groupement alcoxycarbonylphényle, alcoxycarbonyloxyphényle, alcanoylphényle ou N-monoalkylcarbamoylphényle, les restes alkyle dans ces groupements pouvant renfermer jusqu'à 12 atomes de carbone, un reste phényle, thiazolyle ou alkyle en C₁-C₁₂, qui est interrompu éventuellement par 1 à 3 atomes d'oxygène.
  2. Colorants thiazoliques selon la revendication 1 qui répondent à la formule II
    Figure imgb0049
     dans laquelle
    R¹ et R²   représentent chacun, indépendamment l'un de l'autre, un reste alkyle, qui est éventuellement interrompu par 1 à 3 atomes d'oxygène, alcanoyloxyalkyle ou alcoxycarbonylalkyle, ces restes pouvant renfermer jusqu'à 12 atomes de carbone, ou peuvent former ensemble, avec l'atome d'azote qui les relie, un reste hétérocyclique saturé à 5 ou 6 termes qui peut contenir d'autres hétéroatomes,
    L²   représente un atome d'hydrogène ou un reste de formule CONHR¹, NHCOR¹ ou NHSO₂R¹, R¹ ayant chaque fois la signification indiquée précédemment, et
    L³   représente un reste de formule CONHL⁴, NHCOL⁴, SO₂NHL⁴ ou NHSO₂L⁴,
    R³ et L⁴   ayant chacun la signification indiquée dans la revendication 1.
  3. Procédé pour le transfert de colorants du genre des mérocyanines d'un support à un papier revêtu d'une couche de matière plastique au moyen d'une source d'énergie, caractérisé en ce qu'on utilise un support sur lequel se trouvent un ou plusieurs colorants thiazoliques de formule I
    Figure imgb0050
     dans laquelle
    R¹ et R²   sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un reste alkyle, qui est éventuellement interrompu par 1 à 3 atomes d'oxygène, alcanoyloxyalkyle ou alcoxycarbonyloxyalkyle, ces restes renfermant chacun jusqu'à 18 atomes de carbone et pouvant être substitués par des groupements phényle, (alkyl en C₁-C₄)phényle, (alcoxy en C₁-C₄)phényle, hydroxy, cyclohexyle ou cyano, un atome d'hydrogène, un reste phényle éventuellement substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄, un reste cyclohexyle ou un reste de formule



            (CH₂-)kCOO-(Y-O-)m(W-O-)vL¹



    où
    k   est mis pour 2, 3 ou 4
    m et v   sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, pour 0, 1 ou 2,
    Y et W   sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, pour un reste alkylène en C₂-C₆ et
    L¹   est mis pour un reste alkyle en C₁-C₄ ou phényle eventuellement substitué par un reste alkyle en C₁-C₄ ou alcoxy en C₁-C₄,
    ou R¹ et R² forment ensemble, avec l'atome d'azote qui les relie, un reste hétérocyclique saturé à 5 ou 6 termes qui peut contenir d'autres hétéroatomes et être substitué par un reste alkyle en C₁-C₆,
    R³   représente un atome d'hydrogène, d'halogène ou un reste alkyle en C₁-C₈, phényle éventuellement substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄, benzyle éventuellement substitué par un radical alkyle en C₁-C₄ ou alcoxy en C₁-C₄, cyclohexyle, hydroxy, furyle ou thiényle, et
    A   représente un reste de formule
    Figure imgb0051
     où
    L²   est mis pour un atome d'hydrogène, de fluor, de chlore, de brome, pour un reste hydroxy, nitro, alkyle en C₁-C₄, cyano, (alkyl en C₁-C₄)sulfonylamino ou pour un reste de formule COOR¹, CONHR¹, NHCOR¹ ou NHSO₂R¹, R¹ ayant chaque fois la signification indiquée précédemment, et
    L³   est mis pour un atome d'hydrogène, de fluor, de chlore, pour un reste cyano ou pour un reste de formule CONHL⁴, NHCOL⁴, NHCONHL⁴, SO₂NHL⁴, NHSO₂L⁴ ou COOR¹, R¹ ayant la signification indiquée précédemment et L⁴ représentant chaque fois un groupement alcoxycarbonylphényle, alcoxycarbonyloxyphényle, alcanoylphényle ou N-monoalkylcarbamoylphényle, les restes alkyle dans ces groupements pouvant renfermer jusqu'à 12 atomes de carbone, un reste phényle, thiazolyle ou alkyle en C₁-C₁₂, qui est interrompu éventuellement par 1 à 3 atomes d'oxygène.
EP90115763A 1989-08-26 1990-08-17 Colorants thiazoliques du type merocyanine ainsi qu'un procédé de transfert thermique de ces colorants Expired - Lifetime EP0415203B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3928243A DE3928243A1 (de) 1989-08-26 1989-08-26 Merocyaninartige thiazolfarbstoffe sowie ein verfahren zum thermischen transfer dieser farbstoffe
DE3928243 1989-08-26

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EP0415203A2 EP0415203A2 (fr) 1991-03-06
EP0415203A3 EP0415203A3 (en) 1991-08-21
EP0415203B1 true EP0415203B1 (fr) 1994-10-19

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JP (1) JPH0393862A (fr)
DE (2) DE3928243A1 (fr)

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US8377846B2 (en) 2009-06-24 2013-02-19 Eastman Kodak Company Extruded image receiver elements
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US9365067B2 (en) 2013-12-07 2016-06-14 Kodak Alaris Inc. Conductive thermal imaging receiving layer with receiver overcoat layer comprising a surfactant
US9440473B2 (en) 2013-12-07 2016-09-13 Kodak Alaris Inc. Conductive thermal imaging receiving layer with receiver overcoat layer comprising a surfactant
EP3129236B1 (fr) 2014-04-09 2021-09-15 Kodak Alaris Inc. Élément conducteur récepteur de colorant pour l'enregistrement par transfert thermique
CN118574900A (zh) 2022-02-09 2024-08-30 默克专利股份有限公司 经表面处理的金属效果颜料及其制备方法和用途

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EP0415203A2 (fr) 1991-03-06
EP0415203A3 (en) 1991-08-21
JPH0393862A (ja) 1991-04-18
DE3928243A1 (de) 1991-02-28
US5101035A (en) 1992-03-31
DE59007495D1 (de) 1994-11-24

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